Senior Insider Risk Investigator

Wintrust Financial Corporation•Rosemont, IL

1d•$150,000 - $165,000•Hybrid

About The Position

The Senior Insider Risk Investigator serves as the lead investigator for the Insider Risk Program, responsible for leading complex investigations involving data loss, insider threats, policy violations, misuse of company assets, and emerging AI-related risks. This role partners closely with Legal, Human Resources, Privacy, Cybersecurity, and business stakeholders to assess risk, drive appropriate response actions, mentor fellow investigators, and support the continuous maturation of the Insider Risk Program.

Requirements

7+ years of experience in cybersecurity, insider risk, investigations, threat intelligence, digital forensics, incident response, security operations, corporate investigations, or related disciplines
5+ years of experience conducting investigations involving data loss, insider threats, employee misconduct, fraud, abuse of access, policy violations, or other human-centric security risks
Experience managing complex investigations from initial intake through evidence collection, analysis, stakeholder engagement, reporting, and remediation
Experience working with Data Loss Prevention (DLP), Insider Risk Management, SIEM, UEBA, eDiscovery, digital forensics, or related investigative technologies
Experience investigating activity across endpoints, cloud, collaboration, email, identity, and data protection platforms

Nice To Haves

Demonstrated experience analyzing and correlating technical, behavioral, and business-context data to assess risk and support investigative findings.
Experience preparing executive-ready investigative reports, risk assessments, and case summaries for technical and non-technical audiences.
Strong understanding of insider threat methodologies, data protection principles, and human-centric security risks.
Experience conducting threat hunting activities and identifying emerging patterns, trends, and risks through proactive analysis.
Demonstrated ability to mentor, coach, or provide investigative guidance to peers, analysts, or investigators.
Experience operating within highly regulated industries and managing sensitive or confidential employee-related information

Responsibilities

Lead complex insider risk and data loss investigations across email, endpoint, cloud, collaboration, and AI-enabled technologies
Analyze technical, behavioral, and business context to assess risk, intent, and potential impact
Coordinate investigation activities and remediation actions with Legal, Human Resources, Compliance, Privacy, and Cybersecurity teams
Conduct proactive threat hunting activities to identify high-risk behaviors, emerging insider threats, and unauthorized data exposure
Research emerging insider threat, data protection, and AI-related risks to enhance investigative effectiveness and partner with Insider Risk Engineering team to identify monitoring gaps, provide investigative feedback, and improve alert fidelity
Identify opportunities to improve visibility into human-centric risks and strengthen investigative capabilities
Serve as the lead investigator for the Insider Risk Program, providing guidance and mentorship to other investigators sharing investigative knowledge, lessons learned, and emerging threat insights with the team